New Jack was involved in the Mass Transit Incident on November 23, 1996 in Revere, Massachusetts.[1][2][3] The Gangstas were scheduled to face D-Von Dudley and Axl Rotten. Axl, however, never made it to the show for reasons never made clear. (In the 2005 documentary Forever Hardcore, New Jack said he thinks something happened with Axl's grandmother, which forced Axl to not make it). Rotten was replaced with "Mass Transit" Eric Kulas, an untrained seventeen-year-old who convinced bookerPaul Heyman that he was nineteen and had been trained by the veteran Killer Kowalski. Kulas was hospitalized as a result, eventually receiving fifty stitches. New Jack was charged with aggravated assault stemming from the incident, but was acquitted. Kulas subsequently sued New Jack and ECW for damages in July 1998, but lost the case. Kulas died on May 12, 2002 at the age of 22 due to complications from gastric bypass surgery.

New Jack throughout the late-1990s was in a bitter feud with Da Baldies and their leader The Spanish Angel over the unofficial title of "King of the Streets". The two battled back and forth over the matter in bloody street fights. One of ECW television's most gruesome moments is when in the course of a match, Angel used New Jack's staple gun (which he often wore around his neck with a chain) against him, stapling him in the eye. Referees called off the match, and New Jack disappeared from the air for many months. New Jack returned by the end of 1999 with his eye seemingly recovered, now sporting a scythe around his neck, claiming that he had "upgraded" the staple gun. The first match he had against Angel since his return was a successful one, as he continued his feud against Da Baldies.

On March 12, 2000, at the Living Dangerously pay-per-view, New Jack suffered legitimatebrain damage and was permanently blinded in his right eye when he and his opponent, Vic Grimes, fell around fifteen feet off a scaffold, missed the tables that were supposed to absorb the force of their fall and landed on the concrete floor, with Grimes landing on New Jack's head.[4] In a rematch between the two in Xtreme Pro Wrestling (XPW), New Jack threw Grimes from a scaffold (which, this time, was directly above the ring), with Grimes plummeting around thirty feet into the ring. The stunt did not work out as planned, as Grimes only landed on two of the twelve tables that were intended to break his fall and ended up dislocating his ankle on the ring rope. In the 2005 documentary Forever Hardcore, New Jack claimed that he had intentionally thrown Grimes too hard in the hopes that he would hit the ring post and for Grimes to be injured or killed, but under further evaluation Grimes can be seen noticeably pushing off the scaffold with his foot which is one of the main factors leading to the botch. Also in the interview, he said that the Living Dangerously accident was his own fault for prematurely pulling Grimes down from the scaffold. Jack has said that Grimes had been going around telling the locker room that he hurt New Jack, until Jack replied by saying "I hurt me." New Jack also states that he lost eyesight in his right eye from the incident and when his head hit on straight concrete brain fluid was coming out of his nose

In April 2003, New Jack was in a memorable hardcore match with longtime wrestler Gypsy Joe. Joe was continuously no-selling New Jack. New Jack also states on a shoot interview that Joe headbutted him in the nose. This caused New Jack to legitimately attack the sexagenarian with a chain, a framed picture of his aunt, a baseball bat wrapped in barbed wire, and several other weapons. Before the match Jack met Gypsy Joe and went to the booker of the show and asked exactly what he was supposed to do with Joe. Jack was told "Gypsy Joe is as tough as leather", and Jack replied that he was not going to lose dollar value from this match and will not have either a comedy, or a gimmick match, and told the booker he will kill Gypsy Joe in this hardcore match.[5]

In October 2004, New Jack, wrestling for Thunder Wrestling Federation, was scheduled to fight fellow wrestler William Jason Lane. During the match, New Jack pulled out a metal blade from his camouflage wrestling attire, and stabbed Lane fourteen times; This action caused New Jack to receive various felony charges, including for aggravated assault with a deadly weapon, and aggravated assault to commit murder.[6] New Jack claims that the two met prior to the match and agreed to use a "piece of metal" to inflict injury. Despite this, a police officer who was recording the incident stated that it looked like it went "past a routine wrestling match." The promoter of the event, Mr. Maurice Williams, claims the event was never intended to be hardcore. New Jack has claimed that he only stabbed Lane nine times. New Jack announced his retirement on XPW's A Cold Day To Hell in 2008 though he continued working independent shows. In 2012, New Jack competed for Extreme Rising and CZW.

New Jack took part in a shoot interview with The Iron Sheik and The Honky Tonk Man where the subject was Chris Benoit's murder-suicide. New Jack commented that nothing could excuse what Benoit had done and all people on WWE and elsewhere who were making excuses for him were hypocrites. He also thought it was ironic how Extreme Championship Wrestling was seen as violent and dangerous wrestling when he was working there and still only one person died under New Jack's time with the company, whereas WWE was "averaging three a year." (It should be noted that so far five performers, including Benoit, have died while under WWE contract. All five deaths happened within a ten-year period). He also appears in a DVD documentary titled New Jack Hardcore: The History.

New Jack recently made his hip hop recording debut. He contributed several verses to indie rapper Duckman's new album Duckman for Presidente. An animated commercial for the album featuring a cartoon version of New Jack was recently released. New Jack's voice is featured in the commercial and he tells listeners to "buy the cd or I'll stab your ass". In the video game Call of Duty: Modern Warfare 2, the player can earn a call sign titled New Jack, referring to when he stabbed his opponent.[8][9][10]

New Jack has participated in several shoot interviews for RF Video and Kayfabe Commentaries. He was also interviewed by Pro Wrestling Insider for a two-disc DVD set in which he covered his entire career.

New Jack, along with indy wrestler Jay Lover, made an appearance on The Daily Show, on the May 9, 2013 episode of the show, in a segment entitled "Stay Out Of School".[11] It was later confirmed that this was a one-time appearance.[12]